Ammonium Chloride → HCID 11419637, compound

HRID 1062363Notes

Reaction equation

[CH3:1][S-:2].[Na+].[Cl:4][C:5]1[CH:10]=[C:9]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2F)(=[O:13])=[O:12])[CH:8]=[CH:7][C:6]=1[NH:21][C:22](=[O:30])[C@:23]([OH:29])([CH3:28])[C:24]([F:27])([F:26])[F:25].[Cl-].[NH4+]>CN1C(=O)CCC1>[Cl:4][C:5]1[CH:10]=[C:9]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:2][CH3:1])(=[O:13])=[O:12])[CH:8]=[CH:7][C:6]=1[NH:21][C:22](=[O:30])[C@:23]([OH:29])([CH3:28])[C:24]([F:27])([F:26])[F:25]

Participants

Conditions

Temperature: 120 °C

Procedure

Sodium methanethiolate (49.5 mg) was added to a solution of (R)-N-[2-chloro-4-(2-fluorophenylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 63) (0.15 g) in NMP (1.5 ml) and the mixture was heated at 120° C. for 18 hours then cooled. Saturated aqueous ammonium chloride solution (15 ml) was added and the mixture was extracted with ethyl acetate (2×50 ml). The organic extracts were combined, washed with brine and dried. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 0-20% ethyl acetate/hexane to give the title compound (0.10 g) as a solid. NMR: (CDCl3): 1.75 (s, 3H), 2.4 (s, 3H), 3.6 (brs, 1H), 7.3 (t, 1H), 7.35 (t, 1H), 7.55 (m, 1H), 7.9 (dd, 1H), 8.05 (d, 1H) 8.25 (dd, 1H), 8.6 (d, 1H), 9.25 (brs, 1H); MS (ESP−): 452.

Workup

temperaturethen cooled
extractionthe mixture was extracted with ethyl acetate (2×50 ml)
washwashed with brine
customdried
customVolatile material was removed by evaporation
customthe residue was purified by chromatography on a silica gel Mega Bond Elut column
washeluting with 0-20% ethyl acetate/hexane

Sources & evidence

ORD record: ord-6caeec99c15f4585a714e5fd2d9e853a
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960688B2

Reaction notes

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